One reaction which proceeds from a compound with this functional group has been used to synthesize briarelin F in Overland's total synthesis. Prange's total synthesis of forskolin and Chiara's total synthesis of trehazolamine both use Samarium iodide to catalyze cyclizations for producing this functional group. In the latter, a reducing agent donates an electron to produce a radical anion from a carbonyl group and is followed by the formation of a (*) carbon-carbon bond. The mechanism for the latter reaction was elucidated by Butlerov, years after its discovery by Fittig. For 10 points, identify this vicinal diol which lends its name to two reactions, one of which is an acid-catalyzed rearrangement of this compound,
One reaction which proceeds from a compound with this functional group has been used to synthesize briarelin F in Overland's total synthesis. Prange's total synthesis of forskolin and Chiara's total synthesis of trehazolamine both use Samarium iodide to catalyze cyclizations for producing this functional group. In the latter, a reducing agent donates an electron to produce a radical anion from a carbonyl group and is followed by the formation of a (*) carbon-carbon bond. The mechanism for the latter reaction was elucidated by Butlerov, years after its discovery by Fittig. For 10 points, identify this vicinal diol which lends its name to two reactions, one of which is an acid-catalyzed rearrangement of this compound, and the other of which is a coupling reaction that produces this compound.
One reaction which proceeds from a compound with this functional group has been used to synthesize briarelin F in Overland's total synthesis.
{pinacol} [accept {vicinal diol} until “{dihydroxylation}” and prompt {thereafter}; prompt on “{diol}” at any point until “{dihydroxylation}”]